Ben Clymer's fascination with watches started at 16 when his grandfather gave him an Omega Speedmaster right off his wrist. He's since channeled that enthusiasm into the respected and fast-growing watch blog Hodinkee. After we found an old Rolex that turned out to be fake, we asked Clymer about entering the world of vintage watches.

Do your research. There are too many good fakes out there—entire factories in Asia that produce fakes—and if you buy one, your $15,000 investment can become a major loss if you try to sell it. Talk to someone you trust and don't be afraid to get a second opinion. If the dealer has nothing to hide, he'll happily let you show it around.

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What are some things we should be looking for?

If the crown isn't signed, that's a quick indication that something's been toyed with. Also, look at the color of the markers, if they're perfectly white or glow in the dark, and the watch is 50 years old, that doesn't compute. If a dial looks brand new, it probably is.

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Which ones would you recommend?

If you're ready to make the leap, you can't go wrong with the Rolex Submariner Reference 5513 (at left), an Omega Speedmaster Caliber .321, which was the real moon watch, or a Heuer Carrera 2447s.